Sodium Cyanide → 5-(4-Acetyl-3-hydroxy-2-propylphenoxy)pentanenitrile

HRID 543213Notes

Reaction equation

HRID 543213 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12]Br)=[C:6]([CH2:16][CH2:17][CH3:18])[C:5]=1[OH:19])(=[O:3])[CH3:2].[C-:20]#[N:21].[Na+]>CN(C)C=O>[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:20]#[N:21])=[C:6]([CH2:16][CH2:17][CH3:18])[C:5]=1[OH:19])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 133716024-(4-Acetyl-3-hydroxy-2-propylphenoxy)butyl bromide

Product 1

HCID 137633075-(4-Acetyl-3-hydroxy-2-propylphenoxy)pentanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 30.0 g. (91.1 mmoles) of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butyl bromide and 4.91 g. (100.2 mmoles) of sodium cyanide in 225 ml. of dimethylformamide was heated to 75°-85° C. for about 17 hours. The reaction mixture was cooled to room temperature, filtered, and evaporated in vacuo at 75° C. Cold 0.1N hydrochloric acid was added to the residue, and the residue was extracted into ethyl acetate. The ethyl acetate layer was twice washed with 0.1N hydrochloric acid, dried over sodium sulfate, and evaporated in vacuo to yield 21.02 g. of 5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentane nitrile as a dark amber oil which crystallized as it cooled.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo at 75° C
  3. additionCold 0.1N hydrochloric acid was added to the residue
  4. extractionthe residue was extracted into ethyl acetate
  5. washThe ethyl acetate layer was twice washed with 0.1N hydrochloric acid
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto yield 21.02 g
  9. customof 5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentane nitrile as a dark amber oil which crystallized as it
  10. temperaturecooled

Sources & evidence

ORD record
ord-5ea767974e8e472c85d275a7bda32c2a
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

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